Physiologically based biokinetic model of bioactivation and detoxification of the alkenylbenzene methyleugenol in rat

Toxicology in Vitro

Volumn 25, Issue 1, 2011, Pages 267-285

  Al Subeihi, Ala A A ^a,b   Spenkelink, Bert ^a   Rachmawati, Novalia ^a   Boersma, Marelle G ^a   Punt, Ans ^a   Vervoort, Jacques ^a   van Bladeren, Peter J ^a,c   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b BEN HAYYAN Aqaba International Laboratories   (Jordan)

^c NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Bioactivation; Detoxification; In vitro; Methyleugenol; PBBK or PBPK; Rat

Indexed keywords

1' HYDROXYMETHYLEUGENOL; 1' HYDROXYMETHYLEUGENOL GLUCURONIDE; 1' OXOMETHYLEUGENOL; 1' SULFOOXYMETHYLEUGENOL; 2 HYDROXY 4,5 DIMETHOXYALLYLBENZENE; 3 (3,4 DIMETHOXYPHENYL) 2 PROPEN 1 OL; 3 HYDROXY 4 METHOXYALLYLBENZENE; ALKOXYBENZENE DERIVATIVE; CARCINOGEN; EUGENOL; METHYLEUGENOL; METHYLEUGENOL 2',3' OXIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOACTIVATION; CATALYSIS; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEMETHYLATION; DETOXIFICATION; EPOXIDATION; FEMALE; GLUCURONIDATION; HYDROLYSIS; HYDROXYLATION; KIDNEY MICROSOME; LIVER MICROSOME METABOLISM; LUNG; LUNG MICROSOME; MALE; METABOLIC PARAMETERS; METABOLIC RATE; METABOLISM; METABOLITE; MICROSOME; MODEL; NONHUMAN; OXIDATION; PARTITION COEFFICIENT; PHYSIOLOGICALLY BASED BIOKINETIC MODEL; RAT; SENSITIVITY ANALYSIS; SEX DIFFERENCE; STRAIN DIFFERENCE; SULFONATION;

ALKENES; ANIMALS; BIOCATALYSIS; BIOTRANSFORMATION; CARCINOGENS; COMPUTATIONAL BIOLOGY; DOSE-RESPONSE RELATIONSHIP, DRUG; EUGENOL; EXPERT SYSTEMS; FEMALE; KINETICS; MALE; MICROSOMES, LIVER; MODELS, BIOLOGICAL; MUTAGENS; RATS; RATS, INBRED F344; RATS, SPRAGUE-DAWLEY; SEX CHARACTERISTICS; SPECIES SPECIFICITY;

RATTUS;

EID: 78650522818     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2010.08.019     Document Type: Article

References (40)

1. Abdo K.M., Cunningham M.L., Snell M.L., Herbert R.A., Travlos G.S., Eldridge S.R. 14-week toxicity and cell proliferation of methyleugenol administered by gavage to F344 rats and B6C3F1 mice. Food and Chemical Toxicology 2001, 39:303-316.
2. Anthony A., Caldwell J., Hutt A.J., Smith R.L. Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1'-hydroxyestragole. Food and Chemical Toxicology 1987, 25:799-806.
3. Beierschmitt W.P., Weiner M. Age-related changes in renal metabolism of acetaminophen in male Fisher 344 rats. Age 1986, 9:7-13.
4. Borchert P., Wislocki P.G., Miller J.A., Miller E.C. The metabolism of the naturally occurring hepatocarcinogen safrole to 1'-hydroxysafrole and the electrophilic reactivity of 1'-acetoxysafrole. Cancer Research 1973, 33:575-589.
5. Brown R.P., Delp M.D., Lindstedt S.L., Rhomberg L.R., Beliles R.P. Physiological parameter values for physiologically based pharmacokinetic models. Toxicology and Industrial Health 1997, 13:407-484.
6. Campbell D.B. The use of toxicokinetics for the safety assessment of drugs acting in the brain. Molecular Neurobiology 1995, 11:193-216.
7. DeJongh J., Verhaar H.J., Hermens J.L. A quantitative property-property relationship (QPPR) approach to estimate in vitro tissue-blood partition coefficients of organic chemicals in rats and humans. Archives of Toxicology 1997, 72:17-25.
8. De Vincenzi D., Silano M., Stacchini P., Scazzocchio B. Constituents of aromatic plants: I. Methyleugenol. Fitoterapia 2000, 71:216-221.
9. Drinkwater N.R., Miller E.C., Miller J.A., Pitot H.C. Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria. Journal of National Cancer Institute 1976, 57:1323-1331.
10. Evans M.V., Andersen M.E. Sensitivity analysis of a physiological model for 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD): assessing the impact of specific model parameters on sequestration in liver and fat in the rat. Toxicological Sciences 2000, 54:71-80.
11. Fennell T.R., Miller J.A., Miller E.C. Characterization of the biliary and urinary glutathione and N-acetylcysteine metabolism of hepatic carcinogen 1'-hydroxysafrole and its 1'-oxometabolites in rat and mice. Cancer Research 1984, 44:3231-3240.
12. Filser J.G., Faller T.H., Bhowmik S., Schuster A., Kessler W., Putz C., Csanady G.A. First-pass metabolism of 1,3-butadiene in once through perfused livers of rats and mice. Chemico-Biological Interaction 2001, 135-136:249-265.
13. Fisher M.B., Campanale K., Ackermann B.L., Vanden Branden M., Wrighton S.A. In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metabolism Disposition 2000, 28:560-566.
14. Gardner I., Wakazono H., Bergin P., Waziers I., Beaune P., Kenna J.G., Caldwell J. Cytochrome P450 mediated bioactivation of methyleugenol to 1'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Carcinogenesis 1997, 18(9):1775-1783.
15. Garg A., Balthasar J.P. Physiologically-based pharmacokinetic (PBPK) model to predict IgG tissue kinetics in wild-type and FcRn-knockout mice. Journal of Pharmacokinetics and Pharmacodynamics 2007, 34:687-709.
16. Guenthner T.M., Luo G. Investigation of the role of the 2', 3'-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs. Toxicology 2001, 160:47-58.
17. Hall R.L., Oser B.L. Recent progress in the consideration of flavoring ingredients under the food additives amendment III. GRAS substances. Food Technology 1965, 253:151-197.
18. Hissink A.M., Van Ommen B., Kruse J., Van Bladeren P.J. A physiologically based pharmacokinetic (PB-PK) model for 1, 2-dichlorobenzene linked to two possible parameters of toxicity. Toxicology and Applied Pharmacology 1997, 145:301-310.
19. Iyer L.V., Ho M.N., Shinn W.M., Bradford W.W., Tanga M.J., Nath S.S., Green C.E. Glucuronidation of 1'-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9. Toxicological Science 2003, 73:36-43.
20. Jeurissen S.M.F., Bogaards J.J.P., Awad H.M., Boersma M.G., Brand W., Fiamegos Y.C., van Beek T.A., Alink G.M., Rietjens I.M.C.M. Human cytochrome P450 enzyme specificity for bioactivation of safrole to the proximate carcinogen 1'-hydroxysafrole. Chemical Research in Toxicology 2004, 17:1245-1250.
21. Jeurissen S.M.F., Bogaards J.J.P., Boersma M.G., ter Horst J.P.F., Awad H.M., Fiamegos Y.C., van Beek T.A., Alink G.M., Sudholter E.J.R., Cnubben N.H.P., Rietjens I.M.C.M. Human cytochrome P450 enzyme specificity for bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol. Chemical Research in Toxicology 2006, 19:111-116.
22. Lin J.H., Wong B.K. Complexities of glucuronidation affecting in vitro in vivo extrapolation. Current Drug Metabolism 2002, 3:623-646.
23. Luo G., Guenthner T.M. Metabolism of allylbenzene 2', 3'-oxide and estragole 2', 3'-oxide in the isolated perfused rat liver. Journal of Pharmacology and Experimental Therapeutics 1995, 272:588-596.
24. Luo G., Guenthner T.M. Metabolism of allylbenzene 2', 3'-oxide and estragole 2', 3'-oxide in the isolated perfused rat liver. Journal of Pharmacology and Experimental Therapeutics 1996, 272:588-596.
25. Luo G., Qato M.K., Guenthner T.M. Hydrolysis of the 2', 3'-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metabolism and Disposition 1992, 20:440-445.
26. Lupfert C., Reichel A. Development and application of physiologically based pharmacokinetic-modeling tools to support drug discovery. Chemistry and Biodiversity 2005, 2:1462-1486.
27. Medinsky M.A., Leavens T.L., Csanady G.A., Gargas M.L., Bond J.A. In vivo metabolism of butadiene by mice and rats: a comparison of physiological model predictions and experimental data. Carcinogenesis 1994, 15:1329-1340.
28. Miele M., Dondero R., Ciarallo G., Mazzei M.J. Methyleugenol in Ocimum basilicum L.cv. Genovese Gigante. Journal of Agricultural and Food Chemistry 2001, 49:517-521.
29. Miller E.C., Swanson A.B., Phillips D.H., Fletcher T.L., Liem A., Miller J. Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Research 1983, 43:1124-1134.
30. NTP, 2000. Toxicology and carcinogenesis studies of methyleugenol (CAS No. 93-15-12) in F344/N rats and B6C3F1 mice (NTP-TR-491). NIH publication No. 98-3950. National Toxicology Program, Research Triangle Park, NC.
31. Punt A., Delatour T., Scholz G., Schilter B., Bladeren P.J., Rietjens I.M.C.M. Tandem mass spectrometry analysis of N2-(trans-Isoestragol-3'-yl)-2'-deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1'-hydroxyestragole. Chemical Research in Toxicology 2007, 20:991-998.
32. Punt A., Freidig A.P., Delatour T., Scholz G., Boersma M.G., Schilter B., Van Bladeren P.J., Rietjens I.M.C.M. A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicology and Applied Pharmacology 2008, 231:248-259.
33. Punt A., Paini A., Boersma M.G., Freidig A.P., Delatour T., Scholz G., Schilter B., van Bladeren P.J., Rietjens I.M.C.M. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared to male rats. Toxicological Sciences 2009, 110:255-269.
34. Quick D.J., Shuler M.L. Use of in vitro data for construction of a physiologically based pharmacokinetic model for naphthalene in rats and mice to probe species differences. Biotechnology Progress 1999, 15:540-555.
35. Ramsey J.C., Andersen M.E. A physiologically based description of the inhalation pharmacokinetics of styrene in rats and humans. Toxicology and Applied Pharmacology 1984, 73:159-175.
36. SCF, 2001. Opinion of the Scientific Committee on Food on Methyleugenol (4-allyl-1,2-dimethoxybenzene).
37. Smith B., Cadby P., Leblanc J., Setzer R. Application of the margin of exposure (MoE) approach to substances in food that are genotoxic and carcinogenic. Example: Methyleugenol, CASRN: 93-15-2. Food and Chemical Toxicology 2010, 48:S89-S97.
38. Smith R.L., Adams T.B., Doull J., Feron V., Goodman J.I., Marnett L.J., Portoghese P.S., Waddell W.J., Wagner B.M., Rogers A.E., Caldwell J., Sipes I.G. Safety assessment of allylalkoxybenzene derivatives used as flavoring substances methyleugenol and estragole. Food and Chemical Toxicology 2002, 40:851-870.
39. Solheim E., Scheline R. Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers. Xenobiotica 1976, 6:137-150.
40. Tardif R., Droz P.O., Charest-Tardif G., Pierrehumbert G., Truchon G. Impact of human variability on the biological monitoring of exposure to toluene: I. Physiology based toxicokinetics modeling. Toxicology Letters 2002, 134:155-163.